The proposal describes the continued development of allylsilane annulation chemistry in organic synthesis. The [3+2] annulation of allylsilanes is an effective route to the construction of five-member ring carbocycles, however, preparation of enantiomerically pure allylsilanes and participation of functionalized allylsilanes remain significant challenges. The proposal aim is to develop a new method for allylsilane synthesis that allows for facile structural manipulation and numerous enantiomerically pure allylsilanes, as well as, to expand the applications of this methodology by systematically introducing chemically diverse allylsilanes into annulation processes. Once achieved, allylsilane annulation chemistry exponentially increases in synthetic value and significantly raises the number of possible applications in target-driven syntheses.